Ethyl Acetate → 2-(1-Methoxy-cyclopropyl)-2-(4-chlorophenyl)-oxirane

HRID 847162Notes

Reaction equation

HRID 847162 reaction equation
[H-].[Na+].[I-].C[S+](C)(C)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2([O:21][CH3:22])[CH2:20][CH2:19]2)=[O:17])=[CH:12][CH:11]=1.[C:23](OCC)(=O)C>CS(C)=O>[CH3:22][O:21][C:18]1([C:16]2([C:13]3[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=3)[CH2:23][O:17]2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 198824631-Methoxy-cyclopropyl 4-chlorophenyl ketone

Product 1

HCID 198824592-(1-Methoxy-cyclopropyl)-2-(4-chlorophenyl)-oxiraneYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A suspension of 0.82 g (0.0342 mol) of sodium hydride, 7.5 g (0.0342 mol) of trimethylsulphoxonium iodide and 50 ml of dimethyl sulphoxide is initially stirred at room temperature for 30 minutes and then a solution of 6.0 g (0.0285 mol) of 1-methoxy-cyclopropyl 4-chlorophenyl ketone in 10 ml of dimethyl sulphoxide is added at 10° C. After addition is complete, the mixture is warmed to room temperature and stirred for a further 3 hours. 10 ml of ethyl acetate are then added to the reaction mixture and it is stirred for a further 5 minutes. The reaction mixture is poured into ice-water, the resulting mixture is extracted three times with cyclohexane, and the combined organic phases are dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. 5.4 g (84% of theory) of 2-(1-methoxy-cyclopropyl)-2-(4-chlorophenyl)-oxirane are obtained in this manner and reacted further without additional purification. ##STR38##

Workup

  1. additionAfter addition
  2. temperaturethe mixture is warmed to room temperature
  3. stirringstirred for a further 3 hours
  4. stirringis stirred for a further 5 minutes
  5. extractionthe resulting mixture is extracted three times with cyclohexane
  6. dry with materialthe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3596040ae69842a7aceb02f4664d964a
Source dataset
uspto-grants-1992_08
Patent number
US05140035

Reaction notes

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